Starting clerkships is anxiety provoking for medical students. To ease the transition from preclerkship to clerkship curricula, schools offer classroom-based courses which may not be the best model for preparing learners. Drawing from workplace learning theory, the authors developed a seven-day transitional clerkship (TC) in 2007 at the University of California, San Francisco School of Medicine in which students spent half of the course in the hospital, learning routines and logistics of the wards along with their roles and responsibilities as members of ward teams. Twice, they admitted and followed a patient into the next day as part of a shadow team that had no patient-care responsibilities. Dedicated preceptors gave feedback on oral presentations and patient write-ups. Satisfaction with the TC was higher than with the previous year’s classroom-based course. TC students felt clearer about their roles and more confident in their abilities as third-year students compared with previous students. TC students continued to rate the transitional course highly after their first clinical rotation. Preceptors were enthusiastic about the course and expressed willingness to commit to future TC preceptorships. The transitional course models an approach to translating workplace learning theory into practice and demonstrates improved satisfaction, better understanding of roles, and increased confidence among new third-year students.